9-cis-13-trans-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11,13-nonatetraene-15-nitrile | 76985-04-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 9-cis-13-trans-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11,13-nonatetraene-15-nitrile
• 英文别名: (2E,4Z,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenenitrile
• CAS: 76985-04-1
• 化学式: C₂₀H₂₇N
• 分子量: 281.441
• InChiKey: LKTQCZNCSHAYSX-IAGSAMJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-cis-13-trans-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11,13-nonatetraene-15-nitrile 在 吡啶 、 聚合甲醛 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 Acetic acid (1S,6S,7R,8S)-2,6-dimethyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-bicyclo[4.2.0]octa-2,4-dien-7-ylmethyl ester
  参考文献：
  名称：

  Preparation of (9Z, 11Z) - Vitamin A

  摘要：

  Starting from (7E,9Z)-C15-aldehyde 4, the syntheses of (9Z,11Z)-vitamin A acetate and palmitate are reported. The construction strategy is based on treatment of 4 with Zn-PPh3/CBr4, addition of acetaldehyde followed by a Wittig-Horner reaction to give the (9Z,11Z)-C20-nitrile 7 which was reduced with DIBAH to the corresponding aldehyde 8 and then to the title compound 1. The thermal instability of 1 is discussed.

  DOI：

  10.1016/s0040-4039(00)79877-7
• 作为产物：
  描述：

  2-[(1E,3Z)-6,6-dibromo-3-methylhexa-1,3,5-trienyl]-1,3,3-trimethylcyclohexene 在 正丁基锂 作用下， 生成 9-cis-13-trans-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11,13-nonatetraene-15-nitrile
  参考文献：
  名称：

  Preparation of (9Z, 11Z) - Vitamin A

  摘要：

  Starting from (7E,9Z)-C15-aldehyde 4, the syntheses of (9Z,11Z)-vitamin A acetate and palmitate are reported. The construction strategy is based on treatment of 4 with Zn-PPh3/CBr4, addition of acetaldehyde followed by a Wittig-Horner reaction to give the (9Z,11Z)-C20-nitrile 7 which was reduced with DIBAH to the corresponding aldehyde 8 and then to the title compound 1. The thermal instability of 1 is discussed.

  DOI：

  10.1016/s0040-4039(00)79877-7

文献信息

• Zakharova, N. I.; Gutnikova, N. P.; Bekker, A. R., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, p. 1870 - 1874
  作者：Zakharova, N. I.、Gutnikova, N. P.、Bekker, A. R.、Filippova, T. M.、Miropol'skaya, M. A.、Samokhvalov, G. I.

  DOI：——

  日期：——